[Au₂(1,2-bis(dicyclohexylphosphino)ethane)Cl₂] | 99350-06-8

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: [Au₂(1,2-bis(dicyclohexylphosphino)ethane)Cl₂]
• 英文别名: Au2(μ-1,2-bis(dicyclohexylphosphino)ethane)Cl2；[Au₂(dcpe)Cl₂]；Au2(μ-dcpe)Cl2
• CAS: 99350-06-8
• 化学式: C₂₆H₄₈Au₂Cl₂P₂
• 分子量: 887.454
• InChiKey: WSNHUCVAUHWTOI-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  10.65
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  DL-青霉胺 、 [Au₂(1,2-bis(dicyclohexylphosphino)ethane)Cl₂] 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以87%的产率得到
  参考文献：
  名称：

  从介孔型金（I）金属配体与d和l氨基酸的光学纯晶体的创建：一个协调技巧。

  摘要：

  配位技巧：含有d-和1 - penicillamine的中观乙二醛（I）络合物与Co III和M II（Ni II，Zn II）反应生成具有手性（C或A）八面体金属中心的三核络合物。尽管阳离子Au I 2 Co III三核络合物提供了同时包含C和A异构体的外消旋化合物，但中性Au I 2 M II 发现三核配合物通过自发分解产生光学纯的晶体。

  DOI：

  10.1002/chem.201703350
• 作为产物：
  描述：

  1,2-双(二环己基磷基)-乙烷 、 chloroauric acid 在 硫二甘醇 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 [Au₂(1,2-bis(dicyclohexylphosphino)ethane)Cl₂]
  参考文献：
  名称：

  Steric effects and aurophilic interactions in crystals of Au2(μ-1,2-bis(diphenylphosphino)ethane)X2 and Au2(μ-1,2-bis(dicyclohexylphosphino)ethane)X2 (X = Cl, Br, I)

  摘要：

  Crystals in the isostructural series Au-2(mu-dppe)X-2 (dppe is 1,2-bis(diphenylphosphino)ethane, X = CI, Br, I) form centrosymmetric, dimeric structures with two short Au center dot center dot center dot Au contacts between the component molecules. We found no evidence for a second polymorph for any member of the Au-2(mu-dppe)X-2 series, although two polymorphs were observed previously for the related Au-2(Ph2As(CH2)(2)AsPh2)X-2 series. Crystals of Au-2(mu-dcpe)X-2 (where dcpe is 1,2-bis(dicyclohexylphosphino)ethane) show structures that differ appreciably from those of Au-2(mu-dppe)X-2. The bulky cyclohexyl substituents appear to be playing a major role in eliminating the formation of polymeric or dimeric structures. Au-2(mu-dcpe)Cl-2 has a monomeric structure without aurophilic interactions. In contrast, Au-2(mu-dcpe)Br-2 and Au-2(mu-dcpe)I-2 have similar structures with intramolecular aurophilic interactions. Au-2(mu-dcpe)I-2 displays a form of aggregation-induced emission. It displays a red-pink luminescence in crystalline form but is non-emissive in solution. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.06.031

文献信息

• Stepwise Synthesis and Crystal Structure of an Au^I₄Co^III₂ Hexanuclear Complex with <scp>d</scp>-Penicillaminate and Bis(dicyclohexylphosphino)ethane
  作者：Takuma Itai、Tatsuhiro Kojima、Takumi Konno

  DOI：10.1246/bcsj.20170180

  日期：2017.11.15

  The stepwise synthesis of AuI4CoIII2 complex with d-penicillaminate and 1,2-bis(dicyclohexylphosphino)ethane, [2]2+, via metalloligand approach, together with single-crystal X-ray analysis of nitrate salt, [2](NO3)2, is reported. [2](NO3)2 adopts normal alternate arrangement of cations and anions in crystal, which is different from non-alternate arrangement in corresponding AuI4CoIII2 complex with

  通过金属配体方法逐步合成 AuI4CoIII2 配合物与 d-青霉胺和 1,2-双（二环己基膦基）乙烷 [2]2+，以及硝酸盐 [2](NO3) 的单晶 X 射线分析2、被举报了。[2](NO3)2在晶体中采用正负交替排列，这与相应的AuI4CoIII2与d-青霉胺和1,2-双(二苯基膦)乙烷配合物的非交替排列不同。
• Developing Bi-Gold Compound BGC2a to Target Mitochondria for the Elimination of Cancer Cells
  作者：Qingbin Cui、Wenwen Ding、Panpan Liu、Bingling Luo、Jing Yang、Wenhua Lu、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.3390/ijms232012169

  日期：——

  Reactive oxygen species (ROS) homeostasis and mitochondrial metabolism are critical for the survival of cancer cells, including cancer stem cells (CSCs), which often cause drug resistance and cancer relapse. Auranofin is a mono-gold anti-rheumatic drug, and it has been repurposed as an anticancer agent working by the induction of both ROS increase and mitochondrial dysfunction. Hypothetically, increasing auranofin’s positive charges via incorporating more gold atoms to enhance its mitochondria-targeting capacity could enhance its anti-cancer efficacy. Hence, in this work, both mono-gold and bi-gold compounds were designed and evaluated to test our hypothesis. The results showed that bi-gold compounds generally suppressed cancer cells proliferation better than their mono-gold counterparts. The most potent compound, BGC2a, substantially inhibited the antioxidant enzyme TrxR and increased the cellular ROS. BGC2a induced cell apoptosis, which could not be reversed by the antioxidant agent vitamin C, implying that the ROS induced by TrxR inhibition might not be the decisive cause of cell death. As expected, a significant proportion of BGC2a accumulated within mitochondria, likely contributing to mitochondrial dysfunction, which was further confirmed by measuring oxygen consumption rate, mitochondrial membrane potential, and ATP production. Moreover, BGC2a inhibited colony formation and reduced stem-like side population (SP) cells of A549. Finally, the compound effectively suppressed the tumor growth of both A549 and PANC-1 xenografts. Our study showed that mitochondrial disturbance may be gold-based compounds’ major lethal factor in eradicating cancer cells, providing a new approach to developing potent gold-based anti-cancer drugs by increasing mitochondria-targeting capacity.

  活性氧（ROS）平衡和线粒体代谢对包括癌症干细胞（CSCs）在内的癌细胞的存活至关重要，而癌症干细胞往往会导致耐药性和癌症复发。奥拉诺芬是一种单金抗风湿药，它已被重新用作抗癌药，通过诱导 ROS 增加和线粒体功能障碍发挥作用。根据推测，通过加入更多的金原子来增加乌拉诺芬的正电荷，从而提高其线粒体靶向能力，可以增强其抗癌功效。因此，本研究设计并评估了单金和双金化合物，以验证我们的假设。结果表明，双金化合物抑制癌细胞增殖的效果普遍优于单金化合物。最有效的化合物 BGC2a 能显著抑制抗氧化酶 TrxR，增加细胞的 ROS。BGC2a 可诱导细胞凋亡，而抗氧化剂维生素 C 无法逆转细胞凋亡，这意味着抑制 TrxR 所诱导的 ROS 可能不是细胞死亡的决定性原因。正如预期的那样，相当一部分 BGC2a 聚集在线粒体内，很可能会导致线粒体功能障碍，这一点通过测量耗氧率、线粒体膜电位和 ATP 产量得到了进一步证实。此外，BGC2a 还能抑制 A549 的集落形成并减少干样侧群（SP）细胞。最后，该化合物还能有效抑制 A549 和 PANC-1 异种移植的肿瘤生长。我们的研究表明，线粒体干扰可能是金基化合物消灭癌细胞的主要致命因素，这为通过提高线粒体靶向能力开发强效金基抗癌药物提供了一种新方法。
• Creation of Optically Pure Crystals from a Meso‐Type Gold(I) Metalloligand with <scp>d</scp> ‐ and <scp>l</scp> ‐Amino Acids: A Coordination Trick
  作者：Takuma Itai、Tatsuhiro Kojima、Naoto Kuwamura、Takumi Konno

  DOI：10.1002/chem.201703350

  日期：2017.11.21

  A coordination trick: A meso digold(I) complex containing both d- and l-penicillamine reacted with CoIII and MII (NiII, ZnII) to produce trinuclear complexes with chiral (C or A) octahedral metal centers. Though the cationic AuI2CoIII trinuclear complex afforded a racemic compound containing both C and A isomers, the neutral AuI2MII trinuclear complexes were found to produce optically pure crystals

  配位技巧：含有d-和1 - penicillamine的中观乙二醛（I）络合物与Co III和M II（Ni II，Zn II）反应生成具有手性（C或A）八面体金属中心的三核络合物。尽管阳离子Au I 2 Co III三核络合物提供了同时包含C和A异构体的外消旋化合物，但中性Au I 2 M II 发现三核配合物通过自发分解产生光学纯的晶体。
• Steric effects and aurophilic interactions in crystals of Au2(μ-1,2-bis(diphenylphosphino)ethane)X2 and Au2(μ-1,2-bis(dicyclohexylphosphino)ethane)X2 (X = Cl, Br, I)
  作者：Daniel T. Walters、Kellie R. England、Kamran B. Ghiassi、Fikerete Z. Semma、Marilyn M. Olmstead、Alan L. Balch

  DOI：10.1016/j.poly.2016.06.031

  日期：2016.10

  Crystals in the isostructural series Au-2(mu-dppe)X-2 (dppe is 1,2-bis(diphenylphosphino)ethane, X = CI, Br, I) form centrosymmetric, dimeric structures with two short Au center dot center dot center dot Au contacts between the component molecules. We found no evidence for a second polymorph for any member of the Au-2(mu-dppe)X-2 series, although two polymorphs were observed previously for the related Au-2(Ph2As(CH2)(2)AsPh2)X-2 series. Crystals of Au-2(mu-dcpe)X-2 (where dcpe is 1,2-bis(dicyclohexylphosphino)ethane) show structures that differ appreciably from those of Au-2(mu-dppe)X-2. The bulky cyclohexyl substituents appear to be playing a major role in eliminating the formation of polymeric or dimeric structures. Au-2(mu-dcpe)Cl-2 has a monomeric structure without aurophilic interactions. In contrast, Au-2(mu-dcpe)Br-2 and Au-2(mu-dcpe)I-2 have similar structures with intramolecular aurophilic interactions. Au-2(mu-dcpe)I-2 displays a form of aggregation-induced emission. It displays a red-pink luminescence in crystalline form but is non-emissive in solution. (C) 2016 Elsevier Ltd. All rights reserved.